Dawn vs May
by OptimusK
Summary: Dawn and Paul are together untill one night they go to far and Dawn ends up pregnant. Paul then breaks her heart and Dawn is devastated. Ash then comes along picks her right up. Dawn then gets a crush on him but when May already likes him it becomes a battle for Ash's heart. Pearlshipping vs Advanceshipping. Other shipping inside. Rated T for safety.
1. The Characters

**This is a story I plan on making. It is about everyone in high school and Dawn is a popular cheerleader and May is a nerdy bookworm and both end up developing a crush on Ash. Pokemon do not exist in this world. I put up the characters in groups to see what everyone thinks of it. I'm sorry about the title I'm not good a that.  
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**Summary: Dawn and Paul are together untill one night they go to far and Dawn ends up pregnant. Paul then breaks her heart and Dawn is devastated. Ash then comes along picks her right up. Dawn then gets a crush on him but when May already likes him it becomes a battle for Ash's heart. Pearlshipping vs Advanceshipping. Other shipping inside.  
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**Characters**

**Nerds**

Ash Ketchum: Age-16 He is always bullied by the populars only having a few friends. Despite that he is always trying to help people no matter how they are.

May Haruka: Age-16 She is always quite but willing to help people. She had a crush on Ash since sixth grade.

Conway Kohei: Age-16 He is a nerdy stocker knowing everything their is to know about his crush Dawn. Despite being very creepy around Dawn he is a great friend with if givin the chance

Tracey Sketchit: Age-15 He is younger than all his friends but is taller than most of them.

Iris Stevens: Age-16 She is a wild girl and is not held back by anything. She likes Cilan.

Clemont Citron: Age-16 He is Trevor's best friend and the smartest of the group. He is always figuring out solutions for everyone's problems.

Barry Jun: Age-16 He is a hyperactive kid always moving and barely standing still. He is dating Bianca.

Bianca Belle: Age-16 She is like Barry but when she starts running she ends up running into Ash usually sending him into a pool of water. She is dating Barry.

Stephan Kenyan: Age-16 Despite being strong he doesn't want to be part of the popular group as he always hang around with everyone else.

Calem Xavier: Age-16 He is the quiet one of the group only talking when necessary. He is dating Serena.

Serena Saki: Age-16 She used to have the biggest crush on Ash but is now dating Calem.

Shauna Sana: Age-16 She is energetic and is always trying to help May get Ash.

Trevor Trova: Age-16 He always dreams of traveling around the world.

Tierno Haberlorn: Age-16 He is dreams of being the greatest dancer known to anyone.

Brock Stone: Age-18 He is Ash's best friend and he the oldest of the group.

**Populars**

Dawn Hikari: Age-16 She is the head Cheerleader and the most popular girl in the school. She thinks she is in love with her boyfriend Paul.

Paul Shinji: Age-16 He is the most popular guy in the school with his girlfriend Dawn.

Leona Yumomi: Age-15 She is Dawn's best friend and is on the cheerleading squad. She is dating Kenny

Misty Kasumi: Age-17 She is Ash's neighbor and is always picking on him. She is dating Gary.

Gary Oak: Age-16 He used to be Ash's best friend. He is dating Misty.

Cilan Dento: Age-17 He is only popular because his brothers were. He likes Iris.

Red Ketchum: Age-18 Despite being popular he is very nice. He is dating Leaf.

Leaf Green: Age-18 She is dating Red and is the nicest person in the group.

Kenny Kengo: Age-16 He had a crush on Dawn he is currently dating Leona.

Blue Oak: Age-18 He is in a rivalry with Red.

Trip Shooti: Age-16 He always wanted to be a photographer.

**Family**

Delia Ketchum: Age-30 Ash and Red's mother

Johanna Hikari: Age-30 Dawn's mother

Norman Haruka: Age-31 May's father

Caroline Haruka: Age-31 May's Mother

Max Haruka: Age-13 May's younger brother

Bonnie Citron: Age-12 Clemont's younger sister


	2. First Day of School

**Welcome to the first official chapter of Dawn vs May I hope you all like it. I apologize for the long wait but I don't get money off this so I have to have a job so I can get thing to help me live and that cuts into my time to write i'll try to get this out faster next time but no promises.**

**Also with the characters I forgot to mention Dawn's mom Johanna is also the cheerleading he coach. The characters I listed last chapter are only the main ones other ones that I did not list will appear in this story just not as often as the other ones. I got their clothing from Bulbapedia. I forgot to mention Drew and Harley so here are their bio. Drew is part of the populars but Harley is with no one as he is a little to weird to be a popular but hates May and wouldn't be friends with her.**

**Drew Shu: Age- 16 He is arrogant and always in competitions with May. He seems to win most of them causing him to make fun of her and try to make her feel terrible so she wouldn't try to hard the next time they fought.**

**Harley Rannells: Age- 17 He seems to dislike May for some reason as he always laugh the hardest when Drew makes her feel bad. He sometimes get mistaken as a girl.**

" Hey bro get up" said a guy who was dressed in red jacket and normal blue jeans. He is also wearing a red hat with a white brim. "Come on you don't want to be late for the first day of school now would you"

"I'm getting up Red" groggily said the tired boy.

"Well hurry up" the man now known as Red said. He then left the room when the younger boy known as Ash slowly started to get up. When he finally woke up all the way he got dressed in a blue jacket with gold trim and white collar and sleeves, worn open over a dark cyan t-shirt and a pair of normal blue jean **(His Kanto clothing). **When Ash walked down to the kitchen he saw Red eating some eggs and his mother at the counter cooking. His mother is named Delia Ketchum and ever since her husband died she was working as a nurse at the local hospital as a night nurse.

"Morning honey" She said.

"I'm really surprised that you got up in just a few tires as it usually takes awhile to wake you up." said Red.

"Ya but Professor Oak said if i'm late again I'm going to get detention and mom would kill me"

" He's right" said Delia as she was listening to their conversation. "Anyway I got breakfast done so sit and eat Ash then head to school you two."

"Got it mom" Said Ash and Red at the same time.

As they both left the house they saw a redheaded girl wearing a yellow crop top and jean shorts held up with red suspenders and red and white sneakers as she was leaving the house next to them. She looked over and saw Red and Ash. She smiled when she saw Red but frowned when she saw Ash.

"Hey Red" she said.

"Hey Misty" said Red.

"Red I know he's your brother but why do you hang out with this loser" said Misty.

"You know I can hear you" Said Ash..

"So".

"So it not polite to make fun of someone".

"Who cares it just you anyway".

"Misty please try to get along with Ash".

"There's no way I'm going to get along with him he is a loser and why are you even with him".

"I'm with him because he is my brother".

"He's still a loser".

"I'm right here" Ash said angrily.

Misty glared at Ash while him and Red started to walk to school. When they made it they walk to their groups of friends. Ash's best friend is a tall guy with a brown hair. He is wearing a green vest, which had four large pockets on the front. He wore this over an orange short-sleeved shirt, along with brown pants and blue and white sneakers. On either side of his belt, which was black with a gold rectangular buckle, he had attached brown belt pockets.

"Hey Brock" Said Ash

"Hey" The one now known as Brock said.

"Hey Clemont and May"

"Hey" Clemont said. Clemont is a blond boy with a blue and yellow jumpsuit, glasses, and black and white shoes.

"Hi Ash" said May. May is a brunette girl with a red t-shirt with a dark blue circle around her neck, dark blue bike shorts, white skirt, red and yellow sneakers, a red bandanna with a white Ball print.

"So Ash are you ready for professor Oak's class" Said May.

"Why it just another day."

"Um Ash there is a test today." Said Brock.

"THERE IS" screamed Ash

"AW is little Ketchum afraid of a test" Said Misty as she started walking by with Red and a couple of friends first is her boyfriend Gary a brunette boy with a purple shirt with light blue pants. He also has brown shoes. She is also with Dawn a bluenette girl mini dress which is mostly black with a white undershirt inside a V-shaped neck with a short pink skirt. On her head, she wears a white beanie with a pink ball print on it. She also wears gold hair clips that hold up her hair in front. On her feet, she wears pink knee-high boots with black socks underneath. She is holding hand with her boyfriend Paul. He is a boy with purple hair and a purple jacket with a light blue undershirt. He also has gray pants with purple shoes. Rounding off the group is Leaf Red's girlfriend. She is a brunette wearing a white hat with a red stripe and wears a blue and black shirt, red skirt, blue socks and red and white shoes, and two black wristbands.

"Ya Ashy boy" Said Gary.

"Hold on Gary" Leaf started to say.

"Hold on for what Ash here is a loser along with all of his friends. Right Dawn." Said Paul.

"Definitely" agreed Dawn.

Red and Leaf looked over at Ash with apologetic looks. He looked back at them with a look saying its all right.

"Come on everyone why are we even here we should leave before their loserness rubs off on us." Said Misty.

"Hold on we have to use the restroom" Said Leaf and Red together.

"Just make it fast come on lets get to class." Said Paul. They left leaving Leaf and Red with everyone.

"Look i'm sorry about them." Leaf tried to apologise.

"It's alright by the way why are you friends with them. Asked Ash.

"It because Leaf's a cheerleader and I'm captain of the football team." Said Red.

"Ya but that shouldn't make you have to be friends with them" Said Brock.

"Well according to them it does."

"Why can't you just leave" Said May

"Because they aren't that bad"

"Aren't that bad they been trying to make us feel terrible about ourselves since kindergarden" Said May angrily.

"Well" Red started to say.

"Well bye" Said Leaf interrupted Red so he couldn't make May madder than she already was.

Just as they were walking away two more of Ash's friend's showed up first is Conway a green hair guy with a dark green jacket with a light green undershirt. He also wears blue pants and Black sandals. The other one is Tracey a green haired boy with a loose green shirt, reddish-brown shorts and blue and yellow sneakers with an orange backpack with a light red headband.

"Hey was that just Dawn" asked Conway as he looked off towards the way she left.

"Yes and don't try to stalk her or anything" Said Brock.

"What me stalk her"

"Yes you do it everyday"

"I don't stalk her I just watch her every movement very closely."

"Ya because that's not stalking her" Said Ash

"Glad you see it my way" Conway then left to most likely "stalk" Dawn.

"Wow he is very weird why are we friends with him" Said Tracey.

"Ya anyway are you ready for the test" Asked Ash.

"Ya you"

"I didn't know their be one"

"Bummer but don't worry it's the last class of the day." Said Tracey.

"I know how bout I help you out and get you ready for the test" said Brock.

"Thanks Brock "

"No problem" They then left to get to the class where they saw the their friends Serena. She is a honey blond girl wearing a black tank-top with a white collar, a red skirt black long socks, and black shoes. Next to her is her boyfriend Calem as he wears a blue jacket, blue pants, and black boots. Next to them is Iris a purple haired girl with wearing a cream shirt that has long loose sleeves with pink cuffs and a pink collar, a pink skirt with a large pink Ribbon on the side, the pink ribbon is tied around her waist just like a normal cardigan would be also there is white and yellow leggings going over her knees, and pink and white shoes with yellow stripes and a yellow hair Ribbon. Ash looked over and saw Dawn with Paul and two green haired boys one named Drew who is wearing a purple jacket, a dark blue undershirt, light blue pants, and light green shoes. The other is named Cilan who is a lot nicer than the others. He is wearing a white shirt, a black and gray vest with gold buttons, a green bow tie, black pants held up with a brown belt, and brown shoes.

"Hey Iris I know you're staring at Cilan" Said Ash.

"What I wasn't looking at him" Said Iris as she tried to look away blushing.

'It's no use Iris we know you like him." Said Brock as he smiled.

"Why does he always wear that bow tie" Asked Ash.

"I don't know but it make him look so much more sophisticated" sighed Iris.

"Alright everyone get to your seats" said professor Elm. "Now welcome back everyone to history today we are just going over the everything we are doing in the class."

Ash started to drift off on what he was saying thinking how he was going to do this year what he doesn't know is something he will do soon will change everything he knows.

**So now the first official chapter of the story is done. Again I'm sorry about the wait I'll try to be faster next time but again no chapter followed Ash while the next one will follow May then Dawn then back to Ash then so on and so forth. Not much romance in this but next time is May's turn so you can be sure there will be some romance. So until next time thank you for reading and goodbye.**


End file.
